31486-86-9Relevant academic research and scientific papers
Synthesis and evaluation of simple molecule as a co-adsorbent dye for highly efficient co-sensitized solar cells
Zhu, Shengbo,An, Zhongwei,Sun, Xiao,Wu, Zhisheng,Chen, Xinbing,Chen, Pei
, p. 85 - 92 (2015)
One simple-structure dye and two bulky dyes have been designed for exploring a new co-sensitization system utilizing synergy between simple-structure and bulky organic dyes. This small-sized dye molecule can fill up the space defects between bulky dyes, and its strong absorption band from 350 to 500 nm can complement the absorption valleys of the bulky dyes. Additionally, the dye loading of titanium dioxide surface was investigated by Thermogravimetric analysis, which confirms that the molar loading of co-sensitized device has significantly increased. These results exhibit that the simple molecule can be used not only as a co-adsorbent to inhibit charge recombination and π-π aggregation between the bulky dyes but also as a co-sensitizer to improve light-harvesting ability.
A systematic study of the structure-property relationship of a series of nonlinear optical (NLO) julolidinyl-based chromophores with a thieno[3,2-b]thiophene moiety
Zhang, Airui,Xiao, Hongyan,Cong, Shengyu,Zhang, Maolin,Zhang, Hua,Bo, Shuhui,Wang, Qi,Zhen, Zhen,Liu, Xinhou
, p. 370 - 381 (2015)
A series of nonlinear optical (NLO) chromophores a-d bearing thieno[3,2-b]thiophene (TT) as the conjugated bridge or the lateral moiety have been synthesized and investigated. These chromophores display the same julolidinyl-based electron donor, but different electron acceptors (i.e., 2-dicyanomethylene-3-cyano-4-methyl-2,5-dihydrofuran, TCF, or malononitrile). The solvatochromic behavior, thermal stability and electrochemical properties were evaluated to study the structure-property relationships. The solvent dependence of dipole moment (μ), static polarizability (α), hyperpolarizability (β) and bond length alternation (BLA) of all chromophores was demonstrated by density functional theory (DFT) calculations. Upon using the D-A-π-A structure, the blue-shifted phenomenon and substantially enhanced microscopic NLO properties of chromophore d were obtained. The electrooptic coefficient (r33) of chromophore a (94 pm V-1 at 1.31 μm) was four times higher than that of chromophore b (～20 pm V-1), while the calculated hyperpolarizability (β) of chromophore b was five times larger with respect to chromophore a. All the results demonstrated that the TT unit is a highly efficient conjugated bridge, and it has some electronical and sterical effects on macroscopic electrooptic (EO) activity when it is used as the lateral moiety. Guidelines can be proposed for the design of a new series of guest-host polymers including julolidinyl-based chromophores with a TT moiety, which could be useful in organic EO device fabrication. This journal is
Rigid triarylamine-based D-A-π-A structural organic sensitizers for solar cells: The significant enhancement of open-circuit photovoltage with a long alkyl group
Hu, Xiaohao,Cai, Shengyun,Tian, Guojian,Li, Xin,Su, Jianhua,Li, Jing
, p. 22544 - 22553 (2013)
Five new organic D-A-π-A sensitizers DIA6-DIA10 containing benzothiadiazole (BTD) or benzotriazole (BTZ) as auxiliary electron withdrawing units have been synthesized. Their photophysical, electrochemical and photovoltaic properties have been studied. Consequently, although all of these dyes have long alkyl chains grafted on a π-bridge, DSSCs with dyes containing a BTZ unit displayed higher open circuit voltages (757-829 mV) than those containing a BTD unit (682-712 mV). This may be because the nitrogen-based heterocyclic group of BTZ can lift the conduction band edge and reduce the charge recombination that arises from the absence of the sulfur atom. Benefiting from this and the introduction of alkyl chains on the nitrogen atom, DSSCs with one dye containing BTZ and thieno[3,2-b]thiophene (TT) as the π-spacer (DIA7) showed the highest open circuit voltage (Voc = 829 mV). The addition of one more thiophene unit to DIA6 broadens the absorption spectra, leading the DIA8 device to produce the largest photocurrent. Among these sensitizers, the best photovoltaic performance was obtained by the DIA8 device, with a short circuit photocurrent density (Jsc) of 13.45 mA cm -2, an open-circuit photovoltage (Voc) of 757 mV, and a fill factor (FF) of 70%, corresponding to an overall conversion efficiency (η) of 7.15% which reached 93% of the reference dye N719-based cell under standard global AM 1.5 solar light conditions. The Royal Society of Chemistry 2013.
Thieno[3,2-b]thiophene fused BODIPYs: synthesis, near-infrared luminescence and photosensitive properties
Sun, Yijuan,Qu, Zhirong,Zhou, Zhikuan,Gai, Lizhi,Lu, Hua
, p. 3617 - 3622 (2019)
The fusion of π-sufficient heteroaryl moieties has proven to be an effective strategy for achieving the red shift of the main spectral bands of BODIPY. In this paper, thieno[3,2-b]thiophene-fused BODIPY derivatives 1 and 2 have been designed and characterized by various spectroscopic methods, and their photosensitive properties have also been explored. Both dyes absorb in the near-infrared region with extremely high molar extinction coefficients, due to the extension of π-conjugation by fusion of the thieno[3,2-b]thiophene moiety. Their fluorescence quantum yields and singlet oxygen generation properties are significantly affected by iodine substitutions; dye 2 displays a moderate singlet oxygen generation value of 0.32, which makes it a potential NIR photosensitizer for photodynamic therapy of cancer in future research.
Small isomeric push-pull chromophores based on thienothiophenes with tunable optical (non)linearities
Podlesny, Jan,Pytela, Old?ich,Klikar, Milan,Jelínková, Veronika,Kityk, Iwan V.,Ozga, Katarzyna,Jedryka, Jaroslaw,Rudysh, Myron,Bure?, Filip
, p. 3623 - 3634 (2019/04/14)
Fourteen new D-π-A push-pull chromophores based on two isomeric thienothiophene donors and seven acceptors of various electronic natures have been designed and conveniently synthesized. In contrast to known thienothiophene push-pull molecules, the prepared small chromophores proved to be organic materials with easily tunable thermal, electrochemical and (non)linear optical properties. It has also been shown that small structural variation may result in significantly improved/varied fundamental properties. Very detailed structure-property relationships were elucidated within the systematically developed series of push-pull molecules, which may serve as a useful guide in designing new D-π-A molecules based on fused thiophene scaffolds.
Discovery of Potent and Orally Bioavailable GPR40 Full Agonists Bearing Thiophen-2-ylpropanoic Acid Scaffold
Li, He,Huang, Qi,Chen, Cheng,Xu, Bin,Wang, He-Yao,Long, Ya-Qiu
, p. 2697 - 2717 (2017/04/21)
The free fatty acid receptor GPR40 is predominantly expressed in pancreatic β-cells and enhances insulin secretion in a glucose dependent manner. Therefore, GPR40 agonists are possible novel insulin secretagogues with reduced or no risk of hypoglycemia for the treatment of type 2 diabetes mellitus (T2DM). Chemically and structurally diverse GPR40 agonists with high safety are pursued for the clinical development of GPR40-based pharmacotherapeutics. Herein we report our design and discovery of a new chemotype of GPR40 agonists free of the typical phenylpropanoic acid scaffold. The thiophen-2-ylpropanoic acid containing GPR40 modulators functioned as full agonists with high-efficacy response (Emax) and reduced lipophilicity. Significantly, the lead compound in this series, (R)-7k, exhibited more potent in vitro glucose-stimulated insulin secretion and in vivo glucose-lowering effects (10 mg/kg, po) than the GPR40 partial agonist TAK-875, which was once in phase III clinical trials, and high selectivity over the relevant receptors GPR120 and PPARγ.
Synthesis, Fluorescence, and Two-Photon Absorption Properties of Push–Pull 5-Arylthieno[3,2-b]thiophene Derivatives
Manuela,Raposo,Herbivo, Cyril,Hugues, Vincent,Clermont, Guillaume,Castro, M. Cidália R.,Comel, Alain,Blanchard-Desce, Mireille
, p. 5263 - 5273 (2016/11/13)
Three series of novel push–pull 5-arylthieno[3,2-b]thiophene derivatives functionalized with potent electron-withdrawing terminal moieties have been synthesized in moderate to excellent yields by Suzuki coupling followed by Knoevenagel condensation. These novel chromophores show intense absorption in the near-UV region through to the orange visible region, related to a strong intramolecular charge-transfer transition. By combining a strong donor and acceptor, large fluorescence quantum yields were achieved as well as large two-photon absorption responses. Interestingly, due to the improved rigidity and electronic delocalization provided by the thienothiophene moiety (as compared with the bithiophene unit), higher one- and two-photon brightness values have been achieved. As a result, several new fluorescent dyes showing enhanced brightness and tunable fluorescence (ranging from the blue to the NIR region) have been obtained that have potential for bioimaging applications.
Influence of a π-bridge dependent molecular configuration on the optical and electrical characteristics of organic solar cells
Wang, Ting,Han, Liangliang,Wei, Huan,Zhu, Dangqiang,Bao, Xichang,Qiao, Shanlin,Sun, Weizhi,Chen, Weichao,Yang, Renqiang
, p. 8784 - 8792 (2016/07/06)
A new solution processed A-π-D-π-A type small molecule denoted as DCATT-L has been synthesized as a donor for bulk-heterojunction (BHJ) solar cells. Compared with its isomer DCATT, reported in our previous work, DCATT-L possesses the same building blocks, but different π-bridge configurations and hence different backbone configurations. Changing the π-bridge with delicate designs, the absorption coefficient is increased significantly and the highest occupied molecular orbital (HOMO) energy level is decreased by 0.1 eV. The excellent optical and electrical properties of DCATT-L guarantee the enhancement of power conversion efficiency (PCE) to 7.72%, compared with that of DCATT (5.20%), with simultaneously increasing open-circuit voltage, short-circuit current density and fill factor.
Small molecules containing rigidified thiophenes and a cyanopyridone acceptor unit for solution-processable bulk-heterojunction solar cells
Gupta, Akhil,Ali, Abdelselam,Gao, Mei,Singh, Th. Birendra,Bilic, Ante,Watkins, Scott E.,Bach, Udo,Evans, Richard A.
, p. 122 - 132 (2015/05/04)
We designed two solution processable small molecules, 5-((5-(4-(diphenylamino)phenyl)thieno[3,2-b]thiophene-2-yl)methylene)-1-(2-ethylhexyl)-4-methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile (1) and 5-((6-(4-(diphenylamino)phenyl)-4-(2-ethylhex
Elucidating the structure-property relationships of donor-π-acceptor dyes for dye-sensitized solar cells (DSSCs) through rapid library synthesis by a one-pot procedure
Fuse, Shinichiro,Sugiyama, Sakae,Maitani, Masato M.,Wada, Yuji,Ogomi, Yuhei,Hayase, Shuzi,Katoh, Ryuzi,Kaiho, Tatsuo,Takahashi, Takashi
supporting information, p. 10685 - 10694 (2014/11/08)
The creation of organic dyes with excellent high power conversion efficiency (PCE) is important for the further improvement of dye-sensitized solar cells. We wish to describe the rapid synthesis of a 112-membered donor-π-acceptor dye library by a one-pot procedure, evaluation of PCEs, and elucidation of structure-property relationships. No obvious correlations between ε, and the η were observed, whereas the HOMO and LUMO levels of the dyes were critical for η. The dyes with a more positive EHOMO, and with an ELUMOsc, and it was the most important parameter for a high η. The above criteria of EHOMO and E LUMO should be useful for creating high PCE dyes; nevertheless, that was not sufficient for identifying the best combination of donor, π, and acceptor blocks. Combinatorial synthesis and evaluation was important for identifying the best dye. Combinatorial chemistry: A 112-membered donor-π-acceptor dye library was rapidly constructed by a one-pot, three-component coupling procedure (see scheme, SM=Suzuki-Miyaura). The evaluation of absorption spectroscopic and electrochemical measurements of all synthesized dyes, and cell performances of the selected 54 dyes were performed. The dyes with a more positive EHOMO, and with an E LUMO-0.80 V, exerted higher power conversion efficiencies.
